


A Small Problem

by Dbaw3



Series: Adventures of a Pussyboi [1]
Category: Teen Wolf (TV)
Genre: Alternate Universe, Father/Son Incest, Humiliation, M/M, Stiles Stilinski has a Small Dick
Language: English
Status: Completed
Published: 2020-01-03
Updated: 2020-01-03
Packaged: 2021-02-27 06:34:09
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,905
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22102633
Author URL: https://archiveofourown.org/users/Dbaw3/pseuds/Dbaw3
Summary: Stiles has a small problem, and goes to John for advice.Fortunately, John knows it's not a problem at all.
Relationships: Sheriff Stilinski/Stiles Stilinski
Series: Adventures of a Pussyboi [1]
Series URL: https://archiveofourown.org/series/1590907
Comments: 19
Kudos: 498





	A Small Problem

**Author's Note:**

> Originally posted to Tumblr.

John was working at the dining room table when he heard Stiles come in. Stiles was hardly ever what anyone would call stealthy–unless he thought he was actually trying to be sneaky–but he was particularly loud this time, the door slamming on his way in, and so much heavy sighing John thought he might be on the verge of hyperventilating.

John kept his eyes on his papers, knowing what work he needed to get done would likely be over for the night once he engaged with Stiles.

Stiles came to stand in the doorway of the dining room and sighed again. Loudly.

“Date over already?” John asked, not looking up from his papers.

That seemed to be all the permission Stiles needed to release the flailing.

“I don’t get it, Dad!” Stiles yelled, arms waving around in indignation. “I think I’m a good looking guy, right?” 

John sighed and put his pen down, knowing he was not getting back to work any time soon.

“Sure,” John agreed.

“I’m in good shape,” Stiles continued.

“Absolutely,” John said, perhaps more enthusiastically than a father should, but he was biased.

“I’m a nice guy,” Stiles went on.

John was a little less sure of that, but shrugged and said, “Okay.”

Stiles glared, but continued and started pacing. “Then I don’t get it! Two or three dates with a girl are great, but that seems as far as I get!”

John could see where this must be going. He’d been expecting this conversation for years, if he was honest. He’d been pretty certain what Stiles was long before now, but while some experts thought it was better to treat kids like Stiles differently from the beginning, he and Claudia had always thought it might be more natural for Stiles to make his own discoveries. Plus, they’d known their son: there was little you could tell the boy if he wasn’t ready to hear it.

So, here they were, finally going to have this conversation. And John felt himself getting a little hard in his pants already.

“What do you think’s the problem?” John asked carefully, moving his chair out from the table and casually leaning back, noting how Stiles’ eyes darted quickly to his crotch–something he’d been doing more and more lately, John had noticed, which was also why he thought they’d have had this conversation sooner–but still continuing on with his rant.

“I don’t know!” he practically wailed. “We get hot and heavy, things progress along a certain path, and then…pfft!”

“Well, what are you doing when…’pfft!’?” John said, imitating the noise he is making.

Stiles’ eyes go shifty. “Stuff. You know…sexy stuff,” Stiles says cagily.

John proceeds cautiously. “And are you enjoying the…sexy stuff?” he asks casually.

“Of course!” Stiles said instantly, if a little too quickly. “Well, mostly. I don’t know, I figured it’d get better with time. Anyway, that’s not the problem,” Stiles insists, getting himself back on track. “It always seems to happen when I, you know…disrobe,” he says, sort of delicately.

John swallowed around a suddenly dry throat and said simply, “Oh?” trying not to sound too eager in front of his son’s obvious dismay.

Stiles huffed indignantly. “I mean, maybe I’m a grower, not a shower, but I don’t think it’s that bad. I mean, maybe I’m a little…smaller than average, but…” Stiles sort of trailed off, not looking at his dad.

John made a show of sighing. He thought, if he played this right, played this casually enough… “Alright then, show me,” he said, not letting anything but boredom into his voice.

“What?” Stiles said, eyes wide, 

“You’re obviously worried about this,” John said, keeping his voice gentle and his eyes on Stiles’ face, even as he rubbed his own leg near his crotch (which was why he saw Stiles’ eyes dart down and up again). “Show me your size, and I’ll ease your mind about being ‘normal.’“

Stiles hesitated for a second, but reached for his belt with gratifying speed after that. John figured if he was willing to take such a flimsy excuse to expose himself to his father, they were on the right track.

Stiles pulled his pants and underwear down to mid-thigh and pulled up his shirt so John could see clearly what the problem was. 

And it wasn’t as if John hadn’t been expecting this or that he hadn’t been preparing himself for it. It wasn’t as if he wanted to make Stiles feel worse. But he couldn’t help it.

He laughed.

His son’s penis was just so…tiny. Not just “below average” small, but small as in small. John was willing to bet it was at least half hard, and maybe an inch and a half long. It was barely even big enough for John to classify as a penis. Probably because it wasn’t one, he reasoned with an internal shrug as he got control of himself.

Stiles, looking incensed, huffed. “This is what I’m talking about!” he said indignantly.

“I’m sorry,” John said, smiling fondly at his son. “Stop, Stiles,” he said when he saw Stiles starting to cover himself up. He figured it was an excellent sign when Stiles did, standing there with his groin exposed. “Come here, son,” he said, beckoning Stiles closer.

Stiles shuffled nearer to his dad, grumbling under his breath, but not trying to pull his pants back up, until he was near enough for John to place a gentle, reassuring hand on Stiles’ back. 

“Now,” John said, rubbing Stiles’ back and pleased to note when he leaned into his touch. John glanced down to see Stiles’ nub twitch up slightly at his nearness. All of these were excellent signs. “Go ahead and get hard for me,” John instructed.

Stiles startled slightly. “What?”

John sighed, but continued rubbing Stiles’ back, pleased to note Stiles didn’t try to move away. “You want to know if you’re ‘average’ and say you’re ‘a grower,’ you’re going to have to show me what you look like fully hard to judge,” he said reasonably.

“Um, okay,” Stiles said, apparently willing to take this particular bit of logic as an excuse. Stiles began rubbing his little cocklette between his thumb and forefinger for a moment–all he needed to encompass the whole member–but seemed frustrated with it pretty quickly. He moved his hand down down so that his fingers were playing with his balls…then just behind them.

“Um,” Stiles said, blushing or flushed, John couldn’t tell, as he dropped his own hand down to Stiles’ naked waist, Stiles’ breath hitching up. “I can’t…” Stiles trailed off, looking at his father shyly, even as he continued to play with his balls. “I need to touch…somewhere else,” Stiles finished breathlessly and swallowed. “To get really…hard.”

“Go ahead, baby,” John said, patting the top of Stiles’ ass encouragingly, and tried allowing his fingers to linger slightly on the cheeks. John knew he was already leaking into his own shorts. “You do whatever you need to do.”

Stiles smiled, and reached further behind his balls, and even though John tried to keep his eyes on Stiles’ nub, trying to show a detached interest, he knew Stiles was playing with the edge of his own hole, teasing himself with his own fingers, just to make himself fully hard–or as close as he was likely ever to get–for his own father to see.

“Dad,” Stiles gasped out and stopped moving his hand, as if on the verge of something, before pulling it from between his legs. “Um, that’s it.”

“Hm,” John said, and pretended to examine the cocklette in front of him closely. It didn’t take long. At about 2.5″ (generously), it looked much the way it had before Stiles started rubbing himself, like a strange little tube of lipstick, red and hairless, and not much like an adult cock.

“Well, let’s take a look,” John said, and opened his own pants to pull out his dick through the fly, noting his son’s widening eyes and a small drop of precome on the tip of his nub.

“Wow, Daddy,” Stiles said breathlessly. John was sure his son hadn’t even realized his slip from calling him ‘Dad’. “You’re huge. That’s like porn star big,” he said in admiration, eyes wide and glued to his father’s member.

John snorted, but still felt himself puff his chest a bit. “Hardly, boy,” John said, and meant it: He was a good size, he knew, maybe on the larger size of average, but nothing that would shock or amaze most people. He was just growing ever happier that his son wasn’t most people.

“Well, it’s not like I have a lot to compare it to except…” he nodded down to his own inadequate member. “I mean there’s porn, but that’s…well, it’s porn,” he said, obviously indicating the likelihood of that being accurate to reality. “And I mostly hang out with werewolves, so I figured they were throwing the curve, so to speak, but…”

“So, I think you can see,” John said gently, moving so he could compare the obvious differences in their sizes, manouvering Stiles so that he was between John’s legs (”Where he belongs,” John thought to himself briefly). “You won’t be pleasing too many women with that,” he finished, rubbing his hand down further onto his son’s ass to remove any sting of his words, really not trying to hurt his son, but needing to be honest at the same time.

John noticed Stiles starting to chew on his lip, like he usually did when he was feeling anxious, but he was also still staring at John’s erect dick, and John noticed his fingers twitching, as if Stiles was just barely keeping himself from reaching out and….

“Baby,” John said gently, still rubbing Stiles’ back and ass encouragingly, “would you like to touch Daddy’s dick?”

Stiles held his breath for a second and stopped moving, not looking at John’s face, even as John tried to catch his eye. Then, his brave boy gave a brief and shy nod that made John smile.

“It’s okay, honey,” John said gently, and reached for Stiles’s hand, moving it closer to his dick. Stiles took his permission, and lightly touched John’s dick, making it twitch and John gasp before he took a firmer grip and gave it a good stroke.

Stiles’ eyes were even wider now and he said, “Wow, Dad.” and gave John a few more strokes.

John, for the most part, was trying to breathe through his mouth and keep from coming as his boy explored his dick for the first time, making encouraging sounds and noises, wanting Stiles to feel comfortable exploring his cock, taking what he needed, but also not wanting to end this too soon.

Meanwhile, John reached up and cupped his son’s baby balls and rubbed his fingers just behind them causing Stiles to close his eyes with a shudder and gasp, another drop of pre coming to the top of his tiny glans.

“Stiles,” John started, trying to keep his mind on-task of talking to his son rather than his son’s hand on his dick. “Have you ever thought you may be a…pussy?”

Stiles looked up, startled at the word, but didn’t stop stroking John’s dick. “You mean gay? Well, sure, I’ve thought maybe bi, but I don’t think you should use that word…”

John chuckled and cut him off. “No, baby, I don’t mean just gay.” He had continued to rub at Stiles’ balls and perineum, and brought up his thumb to stroke his nub. “I don’t think you’ll find too many gay guys interested in your cute little boyclit, either” he said, not cruelly, and made it wiggle with his thumb. “No, I meant have you ever thought you might be a pussyboi?”

Stiles hesitated, but looked at his father, a dawning realization on his face. “You mean like Uncle Stacy?”

John nodded, pleased his son remembered his uncle. Stacy was Claudia’s brother and a very accomplished pussyboi. Claudia had told John about him discovering his true nature when they were both teenagers and allowing all the men of her family to use him in any way they needed, which was why Claudia had noticed the signs in her own son from a very young age. She’d hoped that eventually Stiles would someday be comfortable enough to come to him and maybe even become John’s personal boi someday. John hadn’t been so sure: there were no pussies in his family, as far as he knew, though of course he’d used them plenty in the dorms at college when he couldn’t find a date, and the volunteer pussies which were made available to his barracks in the army.

Pussybois weren’t that common, but they were considered an incredible asset to any community or gathering, especially in curbing straight men’s appetites and more aggressive nature. Stacy had never hidden who he was–and Claudia insisted John partake of him whenever he visited, both for Stacy’s as well as John’s continued good sexual health–so John knew little Stiles had seen him coming out of the guest bedroom when Stacy visited or even the two of them going into or coming out of the bathroom together more than once. 

Yeah, John remembered Stacy quite fondly. Stacy had joined the Peace Corp several years ago, as some civic-minded pussies sometimes did, being shipped all over the world to impoverished communities which didn’t currently have a pussyboi until a permanent replacement could be found. He remembered how tight and insatiable Stacy had been; once John had even taken him to the Sheriff’s department as a ‘Christmas bonus’ to the deputies who had to be on duty that night. Stacy had gone through everyone on duty and still was able to give a little Christmas cheer to some of the vagrants who were in the holding cells. And he’d still been tight and eager when John came to pick him up the next morning before they headed out to meet Claudia and Stiles for Christmas services.

John suspected, though, that his son was going to be even tighter and more enthusiastic.

”So…” Stiles said, still gripping John’s dick, but now licking his lips as he watched John’s cock start to weep in need. “You think I’m like Uncle Stacy? That’s why my dick is so small?”

Stiles didn’t seem upset by the idea. He actually seemed to be warming to it, almost as if it was a relief.

”Well, it’d be tiny if it were a dick, baby,” John assured him. “But it’s huge if it’s a clit.”Stiles laughed then, possibly in relief, but more with tension. John moved his fingers back slightly, edging them closer to Stiles’ hole. “Baby,” John said, trying to move this along before he shot his load across his son’s hand. Not where he wanted his cum to be this first time, “Tell me. Do you ever get this feeling? Maybe an itch? Down here?” He asked it, and rubbed so that his finger caught just the edge of Stiles’ hole.

Stiles gasped and arched his back, as if searching for more. “Yeah, Daddy. My ass gets so itchy sometimes. How did you know?”

John chuckled, and rubbed his other hand, still on Stiles’ butt, down across both his cheeks, almost covering the entire area with his palm. “This is your ass, baby: not what I was talking about. I meant…here,” and he pushed a finger between Stiles’ cheeks and rubbed directly across his hole for the first time. Stiles whimpered, but bent slightly forward, offering his father more room. Offering his hole.

John, pleased beyond words, pushed his finger in ever so slightly, gentle this first time just in case–but no, there it was, already slick and waiting to be filled. ”Oh, baby, you’re so good. Already wet for your Daddy,” John cooed and pushed his finger all the way in to the first knuckle with ease eliciting a moan from his son. His boi. “Haven’t you wondered why you get wet there?”

Stiles whimpered. “I…I guess so. I just thought something was wrong with me,” Stiles said, pushing back, trying to get more of the finger inside him.

”Oh, baby, there’s nothing wrong with you,” John assured him, and rewarded his son with all of his finger, before pulling it out and pushing it all the way back in. “It just means your hole is a pussy, too.”

”Fuck, Daddy,” Stiles gasped and reached around, as if afraid John would take his hand away. “Please, my hole needs. It needs…” Stiles trailed off, eyes closed, and pushed his ass back onto John’s finger, looking for more.

”It’s not a hole, Stiles, is it?” John said, wanting his son to fully accept what it is, what he was, before going any further. “What is it, baby?”

”My…my pussy,” Stiles said, his eyes opening slightly, and smiling down at John with something close to wonder.

”And what’s this?” John asked, nudging Stiles’ nub again with his thumb. It had gotten plumper and redder, John noticed, but not any longer, since John had inserted his fingers into Stiles.

”My clitty, Daddy,” Stiles said without hesitation.

”Very good,” John praised him. “Does my little boi want me to take care of him now?” John asked, and added a second finger to Stiles’ pussy.

”Oh, fuck, please, Daddy,” Stiles said, and started to ride John’s hand hard.

”What do you want, baby? You gotta say the words so I know what you want?” John insisted. All the books he’d read on this said it was important, this first time, a pussyboi express what they truly needed.

”Daddy, please fuck my pussy with your cock,” Stiles said, and John hooked his fingers inside his boi as a reward.

”Of course, baby,” John said, kissing his son on his lips for the first time. “Daddy will give you what you need.”

Stiles seemed stunned by his father kissing him, more so than any of the other things they’d been doing so far today. John supposed that made sense: even if Stiles was in denial about what he was, he had to know a lot of guys wouldn’t kiss a pussyboi. John kind of understood it, he supposed: he didn’t always kiss the pussybois he’d used in his life, but it seemed polite, if nothing else. And this was his son, and he loved him, as well as wanting in his pussy. 

Stiles might have been surprised, but he got over that quickly, as he suddenly found himself with a lap full of pussyboi, being enthusiastically kissed back.J ohn chuckled, and sucked on his son’s tongue, even as he shared his own. A pussyboi he might be, John thought, as he groaned into his son’s mouth, but he obviously was never going to be one of these passive bois who was just going to lay back and take what a man gave him. John was happy enough with that: he’d always preferred his bois cockhungry and aggressive about it, so it was a good match. Stiles was humping against him, rubbing his clit against John’s cock, which was frustrating them both. John had added a third finger to Stiles’ pussy, and Stiles whimpered, even as he continued to move frantically, searching for something, even if he wasn’t entirely sure what it was.

”Dad, please, I need…” Stiles gasped out between kisses, and John tried to slow him down a little, removing his fingers. Stiles cried out at the loss and pulled back to glare at him. John chuckled, and tried to hold on to his control. 

“I’m not going anywhere, baby,” he assured him, and began to rub the head of his cock against Stiles’ boihole. “Now, this first time, I want you to take it as slow as you…FUCK!!!” John cried out as Stiles slammed his ass down, engulfing John’s cock to the halfway point.

”FUCK!” Stiles echoed, even as he rocked on the dick inside him, moving himself farther and farther down.

John would have admonished him on his language–just because his boi was discovering his pussy didn’t mean he had to have a potty mouth–but he was too busy with his brain exploding and Stiles sliding down his dick. John could always spank him later. And another mini explosion went off in his head at that thought.

”Daddy, daddy, daddy” Stiles chanted and finally settled down, having taken his father all the way to the root.

”Stiles…baby…” John gasped out, knowing he wasn’t going to last long this first time. Wishing he could stay here forever. 

“Daddy,” Stiles said again, and John managed to open his eyes to see Stiles looking at him, pleasure flooding his face, but also a small bit of anxiety. “Is it..okay? Is my pussy good?” he asked.

And if John had had any further doubt that his son was only gay, that cleared it. Only a true pussy would worry about the man’s enjoyment so much more when he had him balls deep in his own hole.

“Your pussy’s perfect, baby,” John assured him truthfully, and cried out as Stiles beamed at him, squeezing down on his cock before rising and falling again.

John lasted longer than he expected to, but it was still only a matter of minutes before he exploded for the first time into his only boi, fucking up roughly into him. He felt more than saw Stiles’ dicklette dribble slightly, but he certainly felt the strong spasms of Stiles’ pussy around his cock, and Stiles experienced the first true boigasm of his life.

Later, when they eventually managed to make it to John’s bed—with a pause for a particularly enthusiastic blowjob in the upstairs hallway, John cooing encouragements as he rubbed his son’s bobbing head the whole time—they were back to Stiles sitting on John’s cock, this time with John propped against the headboard, and Stiles facing out. After multiple orgasms from both of them (Stiles at least four to John’s two, but Stiles was young and pussies always came more, John knew), they were taking this one much more leisurely, Stiles just settling into John’s lap, his legs splayed out to either side of John’s hips. John kissed along his son’s arched neck as Stiles hummed happily.

“Daddy?” Stiles asked, and wow, how much he loved Stiles calling him that, hoped he’d never go back to just “Dad” again. “Do you really think my clit is big?”

John paused after nuzzling his neck a bit more, and looked over Stiles’ shoulder, even as he held his nub between his first and second finger. It had stayed the same length for a while, half-hard and likely to stay that way for the foreseeable future, John knew.

Truthfully, all of the bois John had never known were much bigger than Stiles was. Honestly, Stacy’s clit had been almost five inches long, and he could have stood at a men’s urinal without getting a second glance if he wanted. Not that he did; like most bois, he preferred to pee sitting down.

John hunched his hips up into Stiles, starting the next round of love making, even as he released Stiles’ undersized clit. “Honestly, baby,” John said truthfully, “I think it’s the perfect size.”


End file.
